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Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

Alcohols from Carbonyl Compounds: Reduction

Alcohols from Carbonyl Compounds: Reduction

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...

Metal-Ligand Bonds

Metal-Ligand Bonds

The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

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Related Experiment Video

Updated: Mar 7, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Using Ylide Functionalization to Stabilize Boron Cations.

Thorsten Scherpf¹, Kai-Stephan Feichtner¹, Viktoria H Gessner¹

¹Chair of Inorganic Chemistry II, Faculty of Chemistry and Biochemistry, Ruhr University Bochum, Universitätsstraße 150, 44780, Bochum, Germany.

Angewandte Chemie (International Ed. in English)

|February 11, 2017

Summary

Researchers synthesized stable boron cations using a novel metalated ylide ligand. These boron cations serve as versatile precursors for creating new borenium cations through reactions with Lewis bases like amines.

Keywords:

Lewis acid base pairs boron boron cations carbanions ylide ligands

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Last Updated: Mar 7, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance

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Published on: September 5, 2018

Area of Science:

Organometallic Chemistry
Boron Chemistry
Ligand Design

Background:

Metalated ylides are versatile ligands in coordination chemistry.
Boron cations are reactive intermediates with potential applications.

Purpose of the Study:

To synthesize and characterize novel boron cations stabilized by metalated ylide ligands.
To explore the reactivity of these boron cations with Lewis bases.

Main Methods:

Synthesis of bis-ylide functionalized boron cation [Y-B-Y]+ using metalated ylide YNa and borane.
Characterization using solution and solid-state techniques.
Density Functional Theory (DFT) calculations for stability analysis.

Main Results:

Successful isolation and characterization of the stable bis-ylide functionalized boron cation [Y-B-Y]+.
DFT calculations confirmed stabilization via electrostatic effects and π-donation.
The cation acts as a precursor for other borenium cations.

Conclusions:

The metalated ylide ligand enables the formation of highly stable boron cations.
These cations are valuable synthons for generating diverse borenium species.
Reactions with amines demonstrate N-H activation and tris(amino)borane formation.